I found myself in tears from watching School Days.
It's very sad.
I also found myself questioning my life choices and what I did to deserve this.
But in actually I've never cried in sadness from watching an anime, as in tears trickling down my cheek. I probably would've had I not read Clannad's VN before watching it. There are, however, moments where I've literally shed a tear or two from sheer awesomeness that is the following;
- Code Geass R2's ending
- Tengen Toppa Gurren Lagann's "Who the hell do you think I am?!" final scene
- Fullmetal Alchemist: Brotherhood;